Morpholine hexafluoroarsenate



United States Patent Ofiice 3,l22,53 Patented Feb. 25, 1954 3,122,535 l/ifiRPHQLiIQE HEXAFLUQRGARdENATE Hugh T. Harrison, Midland, Michassignor to The Bow Qhernical Company, Midland, Mich, a corporation ofDelaware No Drawing. Filed lune 4, 1962, Ser. No. l ,622 1 9312553. (Cl.269-242.)

The present invention is directed to the novel compound morpholinehexafiuoroarsenate. The compound corres onds to the formula:

/CHz-CH3 11 N ASFs CHz-CHz H The present compound is a White crystallinematerial, of low solubility in organic solvents and of moderatesolubility in Water. It is useful as a parasiticide, and is adapted tobe employed in the control of insect, bacterial and fungal pests, suchas Musca domestica (house fly).

The novel compound can be prepared by reacting together morpholine andhexafluoroarsenic acid. Couvenienily, the reaction is carried out in aninert liquid reaction medium, such as Water. Good results are obt edwhen substantially equirnolecular proportions or" the reactants areemployed. The reaction is exothermic and takes place smoothly attemperatures of from 15 to 50 C.

In carrying out the reaction, the morpholine is contacte with thehexafiuoroarsenic acid in any conventional manner. The contacting isconveniently carried out by adding one reactant to the other reactant.Ofteutimes it is convenient to employ a hydrate form of the acidreactant. The temperature or the resulting reaction medium can becontrolled by regulating the rate of the contacting of tie reactants asWell as by external cooling. Sometime the desire-J product precipitatesin the mixture during the reaction. Where desirable to maintain fluidcondition such product can in part be separated by conventionalprocedures. Upon completion of the contacting of the reactants, most ofthe reaction will have taken place with the production of the desiredproduct. Where optimum yields are desired, it is often convenient thatthe reaction mixture be allowed to stand several hours to in aresubstantial completion of reaction. Upon completion or" the reaction,the solvent can he removed from the reaction mixture by evaporation ordistillation under reduced pressure to obtain the salt product as aresidue. This product can be further purified by conventional proceduressuch as Washing with water or suitable organic liquid andrecrystallization.

In a representative operation, twenty milliliters (0.23 mole) ofmorphoiine are added portionwise and With stirring to 10% grams ofhexaiiuoroarsenic acid monoiydrate (0.48 mole). The addition is carriedout over a period of rty minutes and at room temperature. Uponcompletion of the addition, the reaction mixture is cooled to atemperature near to 0 C. and the cooled reaction mixture 1- tered toobtain the morpholine hexafluoroarsenate product as a residue. Thisproduct is found to melt at from 212 to 216 C. with decomoosition.

The present compound is useful as a parasiticirle in variousinsecticidal, nematocidal and antimicrobial compositions. For such use,the unmodified compound can be employed. However, the present inventionalso encompasses the use of the compound together with a parasiticideadjuvant. In such use, the compound can be dispersed upon a finelydivided solid and the resulting preparation employed as a dust. Also,such a mixture can be dispersed in Water with the aid of a Wetting agentand the resulting aqueous suspension employed as a spray. In otherprocedures, the product can be employed as a constituent of organicliquid compositions, oilin-water or water-in oil uisions or waterdispersions with or ithout the addion of Wetting, dispersing oremulsifyagents.

In representative operations, aqueous compositions con taining 4000parts by Weight of the subject compound per mfllion parts of compositiongive substantially complete controls or" plum curculio.

I claun:

Morpholine hexafiuoroarsenate.

No references cited.

